Thinking About Dating An Old Friend…Again?


Dating isn’t for the faint of heart, especially when we’ve got some years behind us. And in some ways, more is at stake. Should we give it a try? 

Dating an old friendA close friend of mine dated an upperclassman throughout high school. She married someone else when he got drafted and he married his “war bride.”  Several years later, his wife died and my friend was divorced. 

Another friend fell in love with the boy next door. He took advantage of her innocence then sought her out years later. She turned him down. More years later, he looked her up again.

Is either of these situations conducive to dating?

First, relationships are complicated. When we’re young, we more or less fall into them. However, given a decade to mature, we may see things differently. And with the passing of many years, we may see the very best of all.

Secondly, there were reasons we didn’t stick with that person years ago. Thus, we need to revisit those reasons and see if they’re still valid. Even though there is potential for growth, not everyone allows it to take effect.

Thirdly, we’ve been through a lot, both good and bad, and the other person has also. We can’t assume we’ll appreciate each other’s journey. 

Lastly, we may have add-ons now that didn’t exist when younger. Things like medical and financial issues, an expanded family, changes in faith and struggles with aging.

Don’t assume the voice from the past is a good one–but it may be

Dating an old friend

If we hear negative echoes of a relationship we left behind, perhaps it’s best to play it safe. No dating. 

However, pleasant surprises may also come. After all, that person leaned our way before and we may find a second chance or an open door that never happened.

As for my friend that parted with her high school sweetheart, they met up again while in their forties and spent 35 years together.

My friend that was still being pursued by the neighbor finally found her courage. She shut the door for the last time.

What do you think? Should we give an old flame another shot? Have you?